Acetic Acid → HCID 539410, compound
Reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[Br:6]N1C(=O)CCC1=O.[C:14]([OH:17])(=[O:16])[CH3:15]>>[C:14]([O:17][CH2:1][CH:2]=[C:3]([CH3:4])[CH2:5][Br:6])(=[O:16])[CH3:15]Participants
4
Conditions
- Temperature
- 15 °C
Procedure
Into acetic acid (500 ml) were dissolved 85 g (1.25 mol) of isoprene. Under stirring at 15° C., 260 g (1.45 mol) of N-bromosuccinimide were added therein dividedly four times little by little over two hours. Thereafter, the resulting mixture was stirred for additional two hours. The reaction liquid was added into ice water and extracted with ether. After the organic layer was washed with water, washed with a 5% aqueous solution of sodium hydrogencarbonate, washed with water and dried, the solvent was distilled off. The resulting residue was distilled under reduced pressure, whereby 115 g of the title compound were obtained. (Yield: 52.3%)
Workup
- stirringThereafter, the resulting mixture was stirred for additional two hours
- customThe reaction liquid
- extractionextracted with ether
- washAfter the organic layer was washed with water
- washwashed with a 5% aqueous solution of sodium hydrogencarbonate
- washwashed with water
- customdried
- distillationthe solvent was distilled off
- distillationThe resulting residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-8ad55d739623492397dc34d64a5329f0
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874611
Reaction notes
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